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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H24ClN3O
Molecular Weight 381.898
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZELASTINE, (S)-

SMILES

CN1CCC[C@@H](CC1)N2N=C(CC3=CC=C(Cl)C=C3)C4=C(C=CC=C4)C2=O

InChI

InChIKey=MBUVEWMHONZEQD-SFHVURJKSA-N
InChI=1S/C22H24ClN3O/c1-25-13-4-5-18(12-14-25)26-22(27)20-7-3-2-6-19(20)21(24-26)15-16-8-10-17(23)11-9-16/h2-3,6-11,18H,4-5,12-15H2,1H3/t18-/m0/s1

HIDE SMILES / InChI
Azelastine (brand names AZEP, ASTEPRO, ASTELIN etc.) a phthalazine derivative, is an antihistamine and mast cell stabilizer available as a nasal spray for hay fever and as eye drops for allergic conjunctivitis. Azelastine is a potent antiallergic compound with histamine H1-receptor antagonist activity and a rapid onset and long duration of action. The major metabolite, desmethylazelastine, also exhibits H1- receptor antagonist activity. AZEP Nasal Spray is administered as a racemic mixture. The racemate, R- and S- enantiomers were equally potent at inhibiting eyelid histamine-induced oedema in rats, however the R-enantiomer was 2-fold less active at inhibiting eyeball histamine-induced oedema.

CNS Activity

Curator's Comment: Azelastine is systemically absorbed and can cross the blood–brain barrier. In mice, azelastine showed a definite central action. In rats, a high dose of 100 mg/kg azelastine produced a slight suppression of the paradoxical sleep.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ASTELIN

Approved Use

Astelin Nasal Spray is indicated for the treatment of the symptoms of seasonal allergic rhinitis such as rhinorrhea, sneezing, and nasal pruritus in adults and children 5 years and older, and for the treatment of the symptoms of vasomotor rhinitis, such as rhinorrhea, nasal congestion and postnasal drip in adults and children 12 years and older.

Launch Date

1996
PubMed

PubMed

TitleDatePubMed
Evaluation of the efficacy of olopatadine hydrochloride 0.1% ophthalmic solution and azelastine hydrochloride 0.05% ophthalmic solution in the conjunctival allergen challenge model.
2001 Aug
Mechanism of the antitussive effect of azelastine in guinea pigs.
2002
24-hour efficacy of once-daily desloratadine therapy in patients with seasonal allergic rhinitis [ISRCTN32042139].
2002 Aug 5
Effects of intranasal azelastine on the response to nasal allergen challenge.
2002 Jan
Azelastine's inhibition of histamine and tryptase release from human umbilical cord blood-derived cultured mast cells as well as rat skin mast cell-induced vascular permeability: comparison with olopatadine.
2002 Jan-Feb
Allergic rhinitis remains an important disease.
2002 Jun
Azelastine eye drops in the treatment of perennial allergic conjunctivitis.
2003
Efficacy and safety of topical azelastine compared with topical mitomycin C in patients with allergic conjunctivitis.
2003 Apr
Acute stress results in skin corticotropin-releasing hormone secretion, mast cell activation and vascular permeability, an effect mimicked by intradermal corticotropin-releasing hormone and inhibited by histamine-1 receptor antagonists.
2003 Mar
Antiallergic activity of hesperidin is activated by intestinal microflora.
2004 Aug
Intradermal nociceptin elicits itch-associated responses through leukotriene B(4) in mice.
2004 Jul
Passive cutaneous anaphylaxis-inhibitory activity of flavanones from Citrus unshiu and Poncirus trifoliata.
2005 Jan
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
[Azelastine hydrochloride in the treatment of allergic rhinitis].
2005 Sep
The role of antihistamines in asthma management.
2006
Long QT syndrome in a patient with allergic rhinoconjunctivitis and auto-immune diabetes: focus on the choice of anti-H1 drugs.
2006 Dec
[Comparison of clinical efficacy and cost-quality of antihistamines in early treatment for Japanese cedar pollinosis].
2006 May
Antiallergic drugs, azelastine hydrochloride and epinastine hydrochloride, inhibit ongoing IgE secretion of rat IgE-producing hybridoma FE-3 cells.
2006 Oct 10
Duration of action of topical antiallergy drugs in a Guinea pig model of histamine-induced conjunctival vascular permeability.
2007 Aug
Inhibition of IgE-mediated phosphorylation of FcepsilonRIgamma protein by antiallergic drugs in rat basophilic leukemia (RBL-2H3) cells: a novel action of antiallergic drugs.
2007 Jul
Meta-analysis of azelastine nasal spray for the treatment of allergic rhinitis.
2007 Jun
Azelastine hydrochloride: a review of pharmacology, pharmacokinetics, clinical efficacy and tolerability.
2007 Oct
Efficacy and safety of azelastine nasal spray at a dose of 1 spray per nostril twice daily.
2007 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: To male Wistar rats one single dose of 50 mg/kg AZELASTINE, (S)- was applied orally (by oral gavage): https://www.ncbi.nlm.nih.gov/pubmed/12906914
Adults and children aged 5 years and over: Each spray contains 125 ug of azelastine (as hydrochloride). One spray into each nostril twice daily as necessary (equivalent to a daily dose of 0.50 mg azelastine
Route of Administration: Nasal
In Vitro Use Guide
Curator's Comment: Sensitized cultured human mast cells (CHMCs) were pretreated with various concentrations of azelastine or olopatadine for 5 minutes. Then, CHMCs were challenged with anti-immunoglobulin E (IgE) and the released mediators were quantitated.
The greatest inhibition of mediator release was seen when cultured human mast cells (CHMCs) were pretreated with 24 uM of azelastine.
Name Type Language
AZELASTINE, (S)-
Common Name English
1(2H)-PHTHALAZINONE, 4-((4-CHLOROPHENYL)METHYL)-2-((4S)-HEXAHYDRO-1-METHYL-1H-AZEPIN-4-YL)-
Systematic Name English
Code System Code Type Description
PUBCHEM
12831281
Created by admin on Sat Dec 16 09:02:38 GMT 2023 , Edited by admin on Sat Dec 16 09:02:38 GMT 2023
PRIMARY
FDA UNII
7Y9YE1DOYQ
Created by admin on Sat Dec 16 09:02:38 GMT 2023 , Edited by admin on Sat Dec 16 09:02:38 GMT 2023
PRIMARY
CAS
143228-85-7
Created by admin on Sat Dec 16 09:02:38 GMT 2023 , Edited by admin on Sat Dec 16 09:02:38 GMT 2023
PRIMARY